Startups — and musicians — valued at millions can still fail. 

By Brandy Alexander-Wimberly (Director of Digital Marketing, Interrupt)

I’m a huge Madonna fan. I’ve seen her live multiple times and she always puts on a hell of a show. But lately, she’s been a little, um, off her game, to put it politely.

For those of you who may not be aware, Madonna’s recent tumbles, literally one was a tumble, both happened on stage in front of huge crowds while she was performing.

To summarize: In February while performing at an awards show in London, she somehow got caught up with one of her dancers and fell completely backwards down some steps. The second mishap was last Sunday’s surprise performance at the annual Coachella music fest in California. While on stage performing with Drake, she locked lips with him and afterwards he appeared to be repulsed and gagged. Both of these incidents were of course caught on video and immediately hit the Internet.

Don’t get me wrong. I’m not saying that celebrities are above an occasional wipe out or faux pas. But strategy, planning and flawless execution should always be a goal for any brand, business or public figure.

As I reflected on Madonna’s recent missteps, and found myself even defending her less than stellar behavior to friends, I started to draw a parallel to these mistakes and how early stage founders can potentially learn from them.

1. Knowing Your Audience

Ladies with an attitude, fellas that are in the mood, don’t just stand there, let’s get to it, know your audience, there’s nothing to it. But seriously Madonna, know your audience.

I couldn’t find stats on the average age of Coachella concert goers, but I guarantee it’s not Madonna’s ripe old age of 56. And please, that’s not to say that people in their 50’s can’t be hot and edgy. But it may not play out so well in front of a crowd of people their children’s age. Clearly.

Lot’s of talented artists like Tina Turner and Mick Jagger performed well into this same age and beyond. But they don’t evoke the “ick” factor quite like Madonna does regularly. I’m not saying Madonna should be Betty White, but come on. Show a little sophistication.

Polish, poise and professionalism are just as critical to your success as your concept and path to growth. Don’t carry yourself the same way you do at a bar with friends when you’re networking, presenting your company or pitching investors.

2. Surprising Your Team

From the looks of the video, Drake seemed completely thrown off by Madonna kissing him. If it was planned out, it obviously would have just been part of the act. But apparently Madonna, going for shock value as usual, threw in her own special blend of surprise.

If you’re in client meetings with your team, or similar scenarios, try to stay on the same page. In other words, stop and think it through before throwing a curveball like promising deliverables or committing to anything you haven’t already discussed with your team.

Madonna probably assumed Drake would go with it. Instead she’s having to pay some social media “tax” because of a risky choice, with not that much of a pay-off if it had been better received.

3. Following the Money

Madonna recently announced a concert tour. She’s coming to her hometown of Detroit. Tickets are still available. And if you know anything about past Madonna shows, they used to sell out instantly, especially in Detroit! As a comparison, 50-something Prince recently did a few pop up shows and tickets sold out in seconds. They weren’t even available on Stubhub.

Businesses exist to make money and add value to the people that invest in them and work with them. Period. If your “dream” isn’t paying the bills, consider ditching it for a “dream job” instead and keeping it as a hobby.

4. Letting it Go

Madonna needs to learn the art of moving on. She’s had an impressive run and has done a remarkable job of clutching the spotlight for 30 years. But she’s not like other 1980’s acts that transcend time.

While Madonna and U2 have been apples to apples in terms of longevity, U2’s “act” is much more sustainable. They’re not twerking, nor are they trying to pick fights with up-and-comers. Meanwhile, Madonna calls out Lady Gaga regularly for stealing her act.

If Madonna only realized her second act could be even better than her first, she might actually be worth paying attention to.

Listen Madonna, the whole bad ass bitch thing is played out, you’re tarnishing your legacy!

If you’re holding on to something that clearly isn’t working anymore, let it go. That’s not to say you’ve failed. It means you put on a hell of a good show, learned more than you ever would have without trying and that it’s simply time to try something new.